This will do it on windows: http://www.mediamonkey.com/ http://www.mediamonkey.com/ (I have no vested interest in this company other than continued development

This will do it on windows: http://www.mediamonkey.com/ http://www.mediamonkey.com/ (I have no vested interest in this company other than continued development for my personal use) edit didn't see the comparison below, but this works very well with Iphone/pod/pad